Question 1

Give the best description for the regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene.

Accepted Answer

A)  Markovnikov orientation with syn-addition 
B)  Markovnikov orientation with anti-addition 
C)  Anti-Markovnikov orientation with syn-addition 
D)  Anti-Markovnikov orientation with anti-addition 
E)  Markovnikov orientation with both syn- and anti-addition 
A)  Markovnikov orientation with syn-addition 
B)  Markovnikov orientation with anti-addition 
C)  Anti-Markovnikov orientation with syn-addition 
D)  Anti-Markovnikov orientation with anti-addition 
E)  Markovnikov orientation with both syn- and anti-addition

Question 2

What are the expected major products from the reaction sequence shown below?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 3

When the two constitutional isomers, 3,3-dimethyl-1-butene and 2,3-dimethyl-2-butene, are reacted with HCl the same major product is formed. Provide an explanation for the observation.

Accepted Answer

@#IMG-DLM&_TB4454_00 For the unsymmetrical 3,3-dim

Question 4

Give the expected product(s) resulting from addition of Br2 to (E)-3-hexene.

Accepted Answer

A)  a meso dibromide 
B)  a mixture of optically active enantiomeric dibromides 
C)  a mixture of diasteromeric isomers 
D)  (Z)-3,4-dibromo-3-hexene 
E)  (
E) -3,4-dibromo-3-hexene 
A)  a meso dibromide 
B)  a mixture of optically active enantiomeric dibromides 
C)  a mixture of diasteromeric isomers 
D)  (Z)-3,4-dibromo-3-hexene 
E)  (
E) -3,4-dibromo-3-hexene

Question 5

What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration reaction sequence?

Accepted Answer

A)  Markovnikov addition of H2O, promoting skeletal rearrangement 
B)  Markovnikov addition of H2O, preventing skeletal rearrangement 
C)  anti-Markovnikov addition of H2O, promoting skeletal rearrangement 
D)  anti-Markovnikov addition of H2O, preventing skeletal rearrangement 
E)  anti-Markovnikov addition of H2O, syn-hydroxylation 
A)  Markovnikov addition of H2O, promoting skeletal rearrangement 
B)  Markovnikov addition of H2O, preventing skeletal rearrangement 
C)  anti-Markovnikov addition of H2O, promoting skeletal rearrangement 
D)  anti-Markovnikov addition of H2O, preventing skeletal rearrangement 
E)  anti-Markovnikov addition of H2O, syn-hydroxylation

Question 6

For the following reaction sequence, identify the expected major organic products and provide their stereochemical relationship.

Accepted Answer

A)  I and II; enantiomers 
B)  III and IV; enantiomers 
C)  I and II; diastereomers 
D)  II and III; diastereomers 
E)  III and IV; diastereomers 
A)  I and II; enantiomers 
B)  III and IV; enantiomers 
C)  I and II; diastereomers 
D)  II and III; diastereomers 
E)  III and IV; diastereomers

Question 7

What is the expected major product for the following reaction sequence?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 8

In an addition reaction to an alkene, the π bond is ______.

Accepted Answer

A)  a nucleophile 
B)  an electrophile 
C)  a leaving group 
D)  A and B 
E)  B and C 
A)  a nucleophile 
B)  an electrophile 
C)  a leaving group 
D)  A and B 
E)  B and C

Question 9

For the following reaction draw out the expected major organic product(s). Include regiochemical and/or stereochemical details as relevant, and provide a short justification for the product(s) drawn.

Accepted Answer

@#IMG-DLM&_TB4454_00 The reaction takes

Question 10

What is the expected major product of the following reaction sequence?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 11

The alkene precursor to ethanol is __________.

Accepted Answer

The answer of The alkene precursor to ethanol is __________....

Question 12

Treating 2-methyl-2-pentene with Br2 is expected to produce which of the following as the major product?

Accepted Answer

A)  2,3-dibromo-2-methylpentane 
B)  2,2-dibromo-3-methylpentane 
C)  3,3-dibromo-2-methylpentane 
D)  2-bromo-2-methylpentane 
E)  3-bromo-2-methylpentane 
A)  2,3-dibromo-2-methylpentane 
B)  2,2-dibromo-3-methylpentane 
C)  3,3-dibromo-2-methylpentane 
D)  2-bromo-2-methylpentane 
E)  3-bromo-2-methylpentane

Question 13

Identify the expected major organic product resulting from the following reaction sequence.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 14

Which of the molecules below arises from the anti-Markovnikov hydrohalogenation with HBr of the alkene shown?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 15

For the following dihydroxylation reaction which of the following statements is correct regarding the expected products?

Accepted Answer

A)  Equal amounts of I and II produced 
B)  Equal amounts of III and IV produced 
C)  Equal amounts of I and IV produced 
D)  Equal amounts of II and III produced 
E)  Equal amounts of I and III produced 
A)  Equal amounts of I and II produced 
B)  Equal amounts of III and IV produced 
C)  Equal amounts of I and IV produced 
D)  Equal amounts of II and III produced 
E)  Equal amounts of I and III produced

Question 16

Identify the expected first intermediate formed during a halohydrin reaction.

Accepted Answer

A)  a halonium ion. 
B)  the most stable carbocation with OH on the adjacent carbon. 
C)  the most stable carbocation with X on the adjacent carbon. 
D)  a cyclic oxonium ion. 
E)  the most stable carbanion. 
A)  a halonium ion. 
B)  the most stable carbocation with OH on the adjacent carbon. 
C)  the most stable carbocation with X on the adjacent carbon. 
D)  a cyclic oxonium ion. 
E)  the most stable carbanion.

Question 17

Which of the statements is most correct regarding the products expected from the halogenation reaction shown below?

Accepted Answer

A)  Equal amounts of I and II are produced. 
B)  Equal amounts of III and IV are produced. 
C)  Equal amounts of I and IV are produced. 
D)  Equal amounts of II and III are produced. 
E)  Equal amounts of I and III are produced. 
A)  Equal amounts of I and II are produced. 
B)  Equal amounts of III and IV are produced. 
C)  Equal amounts of I and IV are produced. 
D)  Equal amounts of II and III are produced. 
E)  Equal amounts of I and III are produced.

Question 18

For the following reaction sequence provide the expected major organic product(s). Include all stereoisomers showing relevant stereochemistry.

Accepted Answer

The answer of For the following reaction sequence provide the...

Question 19

Provide the structure(s) of the expected major organic product(s) generated upon completion of the following reaction scheme:

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 20

Which of the following will yield 2-methylpentane upon catalytic hydrogenation?

Accepted Answer

A)  2-methyl-1-pentene 
B)  2-methyl-2-pentene 
C)  4-methyl-2-pentene 
D)  4-methyl-1-pentene 
E)  All of the above 
A)  2-methyl-1-pentene 
B)  2-methyl-2-pentene 
C)  4-methyl-2-pentene 
D)  4-methyl-1-pentene 
E)  All of the above

Exam 8: Addition Reactions of Alkenes

Give the best description for the regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene.

What are the expected major products from the reaction sequence shown below?

When the two constitutional isomers, 3,3-dimethyl-1-butene and 2,3-dimethyl-2-butene, are reacted with HCl the same major product is formed. Provide an explanation for the observation.

Give the expected product(s) resulting from addition of Br2 to (E)-3-hexene.

What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration reaction sequence?

For the following reaction sequence, identify the expected major organic products and provide their stereochemical relationship.

What is the expected major product for the following reaction sequence?

In an addition reaction to an alkene, the π bond is ______.

For the following reaction draw out the expected major organic product(s). Include regiochemical and/or stereochemical details as relevant, and provide a short justification for the product(s) drawn.

What is the expected major product of the following reaction sequence?

The alkene precursor to ethanol is __________.

Treating 2-methyl-2-pentene with Br2 is expected to produce which of the following as the major product?

Identify the expected major organic product resulting from the following reaction sequence.

Which of the molecules below arises from the anti-Markovnikov hydrohalogenation with HBr of the alkene shown?

For the following dihydroxylation reaction which of the following statements is correct regarding the expected products?

Identify the expected first intermediate formed during a halohydrin reaction.

Which of the statements is most correct regarding the products expected from the halogenation reaction shown below?

For the following reaction sequence provide the expected major organic product(s). Include all stereoisomers showing relevant stereochemistry.

Provide the structure(s) of the expected major organic product(s) generated upon completion of the following reaction scheme:

Which of the following will yield 2-methylpentane upon catalytic hydrogenation?

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Give the expected product(s) resulting from addition of Br₂ to (E)-3-hexene.

Treating 2-methyl-2-pentene with Br₂ is expected to produce which of the following as the major product?